JPS59231501A - Plastic lens - Google Patents
Plastic lensInfo
- Publication number
- JPS59231501A JPS59231501A JP58106092A JP10609283A JPS59231501A JP S59231501 A JPS59231501 A JP S59231501A JP 58106092 A JP58106092 A JP 58106092A JP 10609283 A JP10609283 A JP 10609283A JP S59231501 A JPS59231501 A JP S59231501A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- parts
- group
- lens
- colloidal silica
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- G02B1/105—
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/11—Anti-reflection coatings
- G02B1/111—Anti-reflection coatings using layers comprising organic materials
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Abstract
Description
【発明の詳細な説明】
本発明は、合成樹脂によるレンズの表面に優れた耐摩耗
性、耐熱水性、被染色性、耐薬品性、耐候性を有するハ
ードフート膜を施した合成樹脂製レンズに関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a synthetic resin lens in which a hard foot film having excellent abrasion resistance, hot water resistance, stainability, chemical resistance, and weather resistance is applied to the surface of the synthetic resin lens. .
合成樹脂製レンズは、無機ガラスレンズに較べ、軽い、
耐衝撃性に優れる。加工性が良いなど種々の長所を有し
ている０しかし、その反面、傷がつき易いという大きな
欠点があり、さらに有機溶剤に侵され易いという欠点も
ある。Synthetic resin lenses are lighter than inorganic glass lenses.
Excellent impact resistance. However, on the other hand, it has a major drawback of being easily scratched and furthermore being easily attacked by organic solvents.
これらの欠点を改良する方法として、種々の硬化性樹脂
により、レンズを被覆する方法が提案されているが、現
状では、充分満足できるものは得られていない。As a method for improving these drawbacks, methods of coating the lens with various curable resins have been proposed, but at present none of them is fully satisfactory.
たとえば、メチルトリアルコキシ、シランなどの３官能
性シランの加水分解物と、テトラメチルシリテート、テ
トラエチルシリケートなどの４官能性シランの加水分解
物を組み合わせた例が知られているが、耐摩耗性、耐熱
水性、ポットライフなど全ての特性が良好なものはない
。For example, it is known that a hydrolyzate of a trifunctional silane such as methyltrialkoxy or silane is combined with a hydrolyzate of a tetrafunctional silane such as tetramethylsilicate or tetraethylsilicate. There is no one that has good properties in all respects, such as , hot water resistance, and pot life.
また特開昭５１−４２７５２、特公昭５２−１３８１８
、同５３−’１５’７４３にはエポキシ基含有アルコキ
シシランにルイス酸またはそのＭ合体・ブレンステッド
酸、あるいは有機酸の金属塩を硬化触媒として使用する
事が示されているが、これらは塗料のポットライフが短
く、また硬化に長時間を要する為実用的ではない。Also, JP 51-42752, JP 52-13818
, 53-'15'743 discloses the use of a Lewis acid or its M combination, Brønsted acid, or a metal salt of an organic acid as a curing catalyst for an epoxy group-containing alkoxysilane, but these It is not practical because it has a short pot life and takes a long time to harden.
一方特公昭５７−２７３５にはエポキシ基並びにシラノ
ールおよび／またはシロキサン基の両者または一方を含
有する化合物から選ばれた１種または２種以上の混合物
と１〜１００ミリミクロンのシリカ微粒子およびアルミ
ニウムキレート化合物を含有するコーティング組成物が
示されているが、これらの硬化塗膜は硬度が不充分であ
り為熱水浸漬によって硬度の低下が起こる上に、コート
液の寿命が短いという欠点を有している。On the other hand, Japanese Patent Publication No. 57-2735 discloses a mixture of one or more compounds selected from compounds containing both or one of an epoxy group and a silanol and/or siloxane group, silica fine particles of 1 to 100 millimicrons, and an aluminum chelate compound. However, these cured coatings have insufficient hardness, resulting in a decrease in hardness when immersed in hot water, and the coating solution has short service life. There is.
また、合成樹脂製レンズ、特に眼鏡レンズなどにおいて
は・その塗膜が容易に染色されることが望ましく、耐摩
耗性とともに被染色性に対する液のポットライフも重要
となってくる。特開昭５６−９９２６．５には、エポキ
シ基含有アルフキジシランの加水分解物と、ビニル基、
メタクリロキシ基、アミ７基、メルカプト基または塩素
を有するアルコキシシランの加水分解物、粒径１〜１０
０ミリミクロンのコロイダルシリカ、および有機チタン
化合物から選ばれる１種もしくは２種以上、および過塩
素酸アンモニウムを含有するコーティング組成物が示さ
れており、特開昭５７−６７６６５には、（Ａ）ビニル
基、メタクリロキシ基、アミノ基・メルカプト基または
塩素−を有する有機ケイ素化合物、その加水分解物、エ
ポキシ化合物、および分子内に少なくとも１個のエポキ
シを有するビニル単量体を重合または共重合させたポリ
マーまたはコポリマーから選ばれる１種もしくは２種以
上
（Ｂ） 粒径１〜１００ミリミクロンのコロイダルシリ
カ
（０）過塩素酸アンモニウム
を含有するコーティング組成物が示されている。Furthermore, in the case of synthetic resin lenses, especially eyeglass lenses, it is desirable that the coating film be easily dyed, and the pot life of the liquid in terms of stainability as well as abrasion resistance are important. JP-A No. 56-9926.5 discloses a hydrolyzate of epoxy group-containing alfukidisilane, a vinyl group,
Hydrolyzate of alkoxysilane having methacryloxy group, amine 7 group, mercapto group or chlorine, particle size 1 to 10
A coating composition containing colloidal silica of 0 millimicrons, one or more selected from organic titanium compounds, and ammonium perchlorate is disclosed, and JP-A-57-67665 discloses (A) Polymerization or copolymerization of organosilicon compounds having vinyl groups, methacryloxy groups, amino groups, mercapto groups, or chlorine, hydrolysates thereof, epoxy compounds, and vinyl monomers having at least one epoxy in the molecule. A coating composition containing one or more selected from polymers or copolymers (B) colloidal silica (0) ammonium perchlorate having a particle size of 1 to 100 millimicrons is disclosed.
しかし、これらは耐摩耗性と被染色性の両者がともに優
れたものは得られず、被染色性自体もポットライフによ
って刻々と変化する為実用性は低い。However, these methods do not have excellent abrasion resistance and dyeability, and the dyeability itself changes from moment to moment depending on the pot life, so they are of low practical use.
本発明者らは、かかる欠点を除去し、耐摩耗性、耐熱水
性、安定した被染色性、耐薬品性、耐候性に優れた合成
樹脂製レンズを得るべく研究を重ねた結果、本発明に至
った。The present inventors have conducted repeated research to eliminate such drawbacks and obtain a synthetic resin lens with excellent abrasion resistance, hot water resistance, stable stainability, chemical resistance, and weather resistance, and as a result, the present invention has been developed. It's arrived.
すなわち、本発明は合成樹脂レンズ表面に、下記（ハ）
） 、 （Ｂ） 、 （０）及び（Ｄ）（式中Ｒ１は炭
素数１〜乙の炭化水素基、ビニル基、メタクリロキシ基
またはエポキシ基を有する有機基、Ｒ２は炭素数１〜４
の炭化水素基、Ｒ３は炭素数１〜５の炭化水素基。That is, the present invention provides the following (c) on the surface of a synthetic resin lens.
), (B), (0) and (D) (in the formula, R1 is an organic group having a hydrocarbon group having 1 to 4 carbon atoms, a vinyl group, a methacryloxy group, or an epoxy group, and R2 is an organic group having 1 to 4 carbon atoms)
R3 is a hydrocarbon group having 1 to 5 carbon atoms.
７ ／ｌｚコキシルアルキル基または水素原子、ｎは０
または１を表わす）で示される有機ｔイ素化合物の１種
もしくは２種以上、
（Ｂ）粒径１〜１００ミリミクロンのコロイダルシリカ
（０）多官能性エポキシ化合物
（Ｄ）過塩素漕マグネシウム
を主原料としてなるハードコート膜を施した合成樹脂製
レンズである。7/lz coxyl alkyl group or hydrogen atom, n is 0
or 1); (B) colloidal silica with a particle size of 1 to 100 millimicrons; (0) polyfunctional epoxy compound; (D) perchlorine tank magnesium; This is a synthetic resin lens coated with a hard coat film, which is the main raw material.
本発明で用いられる成分（Ａ）としては、メチルトリメ
トキシシラン、エチルトリエトキシシラン。Component (A) used in the present invention includes methyltrimethoxysilane and ethyltriethoxysilane.
メチルトリエトキシシラン、フェニルトリメトキシシラ
ン、ジメチルジメトキシシラン、フェニルメチルジメト
キシシラン、ビニルトリエトキシシラン、ビニル−トリ
ス（β−メトキシエトキシ）シラン、ビニルトリアセト
キシシラン、）γ−グリシドキシプロビルトリメトキシ
シラン、ｒ−グリシドキシプ四ビルメシルジェトキシシ
ラン、β−（３，４エポキシシクロヘキシル）エチルト
リメトキシシラン等がある。またこれらは、アルコール
等の有機溶剤中、酸の存在下で力ロ木分解して使用する
方が好ま一シく、単独で加水分解後に成分（Ｂ）のコロ
イダルシリカと混合しても、成分（Ｂ）と混合後に加水
分解をしても、いずれでも良い。Methyltriethoxysilane, phenyltrimethoxysilane, dimethyldimethoxysilane, phenylmethyldimethoxysilane, vinyltriethoxysilane, vinyl-tris(β-methoxyethoxy)silane, vinyltriacetoxysilane, )γ-glycidoxypropyltrimethoxy Examples include silane, r-glycidoxyptetravirmesyljethoxysilane, and β-(3,4 epoxycyclohexyl)ethyltrimethoxysilane. In addition, it is preferable to use these by hydrolyzing them in the presence of an acid in an organic solvent such as alcohol, and even if they are used alone after hydrolysis and then mixed with the colloidal silica of component (B), It may be hydrolyzed after mixing with (B) or it may be hydrolyzed.
成分（Ｂ）の粒径１〜１００ミリミクロンのコロイダル
シリカとは、水またはアルコール系の分散媒に、高分子
量の無機ケイ醗微粒子を分散したコロイド溶液であり、
市販されているものである。Component (B) colloidal silica having a particle size of 1 to 100 millimeters is a colloidal solution in which high molecular weight inorganic silicon fine particles are dispersed in a water or alcohol dispersion medium,
It is commercially available.
成分（Ｃ）の多官能性エポキシ化合物としては、（ポリ
）エチレングリコール、（ポリ）プロピレングリコール
、ネオペンチルグリコール、カテコール、レゾルシノー
ル、アルキレングリコールなどの二官能性アルコールの
ジグリシジルエーテル、または、グリセリン、トリメチ
ロールプロパンなどの三官能性アルコールのジまたはト
リグリシジルエーテルなどがあげられる。As the polyfunctional epoxy compound of component (C), diglycidyl ethers of difunctional alcohols such as (poly)ethylene glycol, (poly)propylene glycol, neopentyl glycol, catechol, resorcinol, and alkylene glycol, or glycerin, Examples include di- or triglycidyl ethers of trifunctional alcohols such as trimethylolpropane.
成分（Ａ）の１種もしくは２種以上、成分（Ｂ）および
成分（０）に硬化触媒として成分（Ｄ）の過塩素酸マグ
ネシウムを使用することにより、優れた耐熱水性、被染
色性、耐薬品性＼耐候性を有する塗膜を与え、かつ、ポ
ットライフの極めて長い塗料を得ることができる。By using magnesium perchlorate (component (D)) as a curing catalyst for one or more components (A), component (B), and component (0), excellent hot water resistance, dyeability, and resistance can be achieved. It is possible to obtain a paint film that is chemically resistant and weather resistant and has an extremely long pot life.
次に成分（Ｄ）の過塩素酸マグネシウムについて説明す
る。Next, component (D) magnesium perchlorate will be explained.
一般忙、シラノールあるいはエポキシ基の硬化触媒とし
ては、以下のようなものが知られているが）各々以下に
あげるような欠点を有する。すなわち、ｎ−ブチルアミ
ン、トリエチルアミン、グアニジン、ビグアニドなどの
アミン、グリシンなどのアミノ酸などは、硬度が不充分
であり、アルミニウムアセチルアセトネート、クロムア
セチルアセトネート、チタニルアセチ尻アセトネート、
コバルトアセチルアセトネートなどの金属アセチルアセ
トネートも硬度が出に＜＜、あるいは、ある程度の硬度
が出た場合にも、耐水性が悪い為、熱水浸漬によって硬
度の低下が起こり、スポットライフも短い。また、酢酸
ナトリウム、ナフテン酸亜鉛・す７テン酸コバルト、オ
クチル酸亜鉛、オクチル酸スズなどの有機酸金属塩、過
塩素酸などは、塗料のポットライフが短く、過塩素酸ア
ンモニウムは被染色性がばらつき、塗料のライフに ・
“よっても被染色性が変化する為、実用的でない。The following are known as general curing catalysts for silanol or epoxy groups, but each has the following drawbacks. That is, amines such as n-butylamine, triethylamine, guanidine, biguanide, amino acids such as glycine, etc. have insufficient hardness, and aluminum acetylacetonate, chromium acetylacetonate, titanyl acetylacetonate,
Metallic acetylacetonates such as cobalt acetylacetonate also exhibit hardness <<, or even if they do develop a certain degree of hardness, they have poor water resistance, so immersion in hot water causes a decrease in hardness and short spot life. . In addition, organic acid metal salts such as sodium acetate, zinc naphthenate, cobalt heptathenate, zinc octylate, tin octylate, and perchloric acid have a short pot life, and ammonium perchlorate has a tendency to stain.・The life of the paint will be affected.
“However, it is not practical because the dyeability changes.
ざうに、塩ＷＩ、リン酸、硝酸、パラトルエンスルホン
酸などは、硬化に長時間を要し、５ｎＯＱ。。Zanuni, salt WI, phosphoric acid, nitric acid, para-toluenesulfonic acid, etc. take a long time to cure and have a 5nOQ. .
Ａｊ２ａｊ２． 、ＦＩＩＣＡ３ 、Ｔｉ０１１． 、
Ｚｎ０１ｔ２，５６ｃＡ。Aj2aj2. , FIICA3, Ti011. ,
Zn01t2,56cA.
などのルイス酸は、得られる塗膜が極めて耐水性が悪い
為、常温で水中浸漬により硬度が低下する。Lewis acids such as these produce coating films with extremely poor water resistance, and their hardness decreases when immersed in water at room temperature.
以上の結果より、本発明者らは種々の硬化触媒について
検討を重ねた結果、潜在性触媒の一種である過塩素酸マ
グネシウムがあらゆる特性についても優れていることを
見いだした。すなわち、塗料の実用可能なポットライフ
は室温保存で１ケ月以上であり、得られる塗膜の耐摩耗
性、耐熱水性、耐薬品性、被染色性、耐候性も優れたも
のである。Based on the above results, the present inventors have repeatedly investigated various curing catalysts and have found that magnesium perchlorate, which is a type of latent catalyst, is excellent in all properties. That is, the practical pot life of the paint is one month or more when stored at room temperature, and the resulting paint film has excellent abrasion resistance, hot water resistance, chemical resistance, stainability, and weather resistance.
本発明において使用される各成分の混合量は、好ましく
は、成分（１３）（ｓｔｏ２として一計算した固形分）
１００重量部に対して、成分（Ａ）の合計が５０計算し
た固形分に換算）、成分（０）が５０〜６００重量部、
より好ましくは成分（Ａ）が５０〜５００重量部、成分
（０）は１００〜５００重量部である０さらに成分（Ｄ
）は、全残留固形分の０．０１〜５．０％の範囲内で使
用することが望ましい。The mixing amount of each component used in the present invention is preferably component (13) (solid content calculated as sto2)
For 100 parts by weight, the total of component (A) is 50 (calculated solid content), component (0) is 50 to 600 parts by weight,
More preferably, component (A) is 50 to 500 parts by weight and component (0) is 100 to 500 parts by weight.
) is desirably used within the range of 0.01 to 5.0% of the total residual solid content.
また、アルコール類、ケトン類、セロソルブ類１カルボ
ン酸類などの溶媒を単独または混合して加えることもで
き、必要に応じて、少量の界面活性剤、帯電防止剤、紫
外線吸収剤を添加し、コート液の塗布性・コート膜の性
能を改良することもできる。In addition, solvents such as alcohols, ketones, and cellosolve 1 carboxylic acids can be added alone or in combination, and if necessary, small amounts of surfactants, antistatic agents, and ultraviolet absorbers can be added to coat the coating. It is also possible to improve the coating properties of the liquid and the performance of the coating film.
なお、本発明はさまざまな合性樹脂に適用でき・密着性
の悪いものは、プライマー処理をすることによって高度
の密着性が得られる。The present invention can be applied to various synthetic resins. For those with poor adhesion, a high degree of adhesion can be obtained by applying a primer treatment.
以下、実施例に基づいて本発明の詳細な説明するが、本
発明はこれらに限定されるものではない。Hereinafter, the present invention will be described in detail based on Examples, but the present invention is not limited thereto.
実施例−１
（１）塗料調整および塗布
ｌチルトリメトキシシラン１０８重量部、イソプロパツ
ール分散コロイダルシリカ（触媒（ＥＪｊＥ工業（株）
製”０ＳＯＡＬ−１４３２”、固形分濃度３０％） ２
１２ ＭＩｋ部およびイソプロパツール４５９重量部か
らなる溶液に、０．０５規定（Ｎ）塩酸５２重量部を徐
々に滴下し・加水分解を行なった。Example-1 (1) Paint preparation and application l 108 parts by weight of tiltrimethoxysilane, isopropanol-dispersed colloidal silica (catalyst (EJJE Kogyo Co., Ltd.)
"0SOAL-1432" manufactured by Manufacturer, solid content concentration 30%) 2
To a solution consisting of 12 parts by weight of MIk and 459 parts by weight of isopropanol, 52 parts by weight of 0.05N hydrochloric acid was gradually added dropwise to perform hydrolysis.
この溶液を０２℃で２４時間熟成した後、１，６−ヘキ
サンシオールジグリシジルエーテル（共栄社油脂（株）
製６エポライト１６００１′）１８３重量部と過塩素酸
マグネシウム５重量部を室温で加え、攪拌して均一とし
た。これにさらに、フローコントロール剤（日本ユニカ
ー（株）製”Ｌ−７６０４”）を数滴加えて塗料を調製
した。この液に、あらかじめ４％水酸化ナトリウム水溶
液で表面処理し洗浄乾燥した（！Ｒ−５９レンズを浸漬
し、毎分２０偏の速さで引き上げて塗布し、８０℃で１
時間、１３０℃で１時間加熱し硬化させた。After aging this solution at 02°C for 24 hours, 1,6-hexanethiol diglycidyl ether (Kyoeisha Yushi Co., Ltd.)
6 Epolite 16001') and 5 parts by weight of magnesium perchlorate were added at room temperature and stirred until the mixture was homogeneous. Further, several drops of a flow control agent ("L-7604" manufactured by Nippon Unicar Co., Ltd.) were added to prepare a paint. In this solution, the surface was previously treated with a 4% sodium hydroxide aqueous solution, washed and dried (!R-59 lens was immersed in the solution, and was applied by pulling it up at a speed of 20 degrees per minute.
The film was cured by heating at 130° C. for 1 hour.
（２） 性能評価試験
耐摩耗性： １２の＊ｏｏｏｏスチールウール（日本ス
チールウール（株）製）に１９荷重をかけ、１０往復こ
すった時の傷の着き具合をガラスをＡ１アクリル樹脂を
Ｅ′として１０段階で評価した。(2) Performance evaluation test Abrasion resistance: Applying a load of 19 to 12*oooo steel wool (manufactured by Nippon Steel Wool Co., Ltd.) and rubbing it back and forth 10 times. It was evaluated on a scale of 10 to 10.
耐熱水性： レンズを沸騰している純水に１時間浸漬し
た後、前記と同様に耐摩耗性の試験を行なったＯ
被染色性＝ ９５℃９５０ｗＬｌの純水に、ＢＰＩ製Ｇ
ＲＡＹ染色剤１本を溶がし染色液を調整した＠この液に
・レンズを１０分間浸漬し染色して、５１０請の単色光
の透過率を測定した。Hot water resistance: After immersing the lens in boiling pure water for 1 hour, the abrasion resistance test was conducted in the same manner as above.
A dyeing solution was prepared by dissolving one bottle of RAY dye.The lens was immersed in this solution for 10 minutes to be dyed, and the transmittance of monochromatic light of 510 degrees was measured.
耐薬品性： ４％水酸化す） ｌ）ラム水溶液中に１時
間浸漬後のレンズの外観および１０％塩酸中に２４時間
浸漬後の外観で評価した。Chemical resistance: (4% hydroxide) l) The appearance of the lens after being immersed in a rum aqueous solution for 1 hour and the appearance after being immersed in 10% hydrochloric acid for 24 hours was evaluated.
耐候性： キノンランプフェードメーターで紫外線照射
５００時間後の塗膜の外観で評価した。Weather resistance: Evaluated by the appearance of the coating film after 500 hours of ultraviolet irradiation using a quinone lamp fade meter.
各評価結果を表−１に示した。The results of each evaluation are shown in Table-1.
実施例−２
メチルトリメトキシシラン１１１重量部、メタノール分
散コロイダルシリカ（触媒化成工業Ｃ株）製”０８ＯＡ
Ｌ−１１５２’、固形分濃度５０％）２７１重量部およ
びイソプロパツール３９５重量部からなる溶液に、０．
０５ Ｎ塩酸５３重量部を徐々に滴下し、加水分解を行
なった。この溶液を０℃で２４時間熟成した後、トリメ
チロールプロパ ゛ントリグリシジルエーテル（共栄
社油脂（株）製１エボライ）１００ＭＦ”）１６４重量
部と過塩素酸マグネシウム５重量部を室温で加え、攪拌
して均一とした。これに、フローコントロール剤Ｌ−７
６０４を数滴加えて塗料を調整した。レンズの処理およ
び塗布の方法は実施例−１と同じである。Example-2 111 parts by weight of methyltrimethoxysilane, methanol-dispersed colloidal silica (Catalyst Chemical Industry Co., Ltd.) "08OA"
To a solution consisting of 271 parts by weight of L-1152' (solid content 50%) and 395 parts by weight of isopropanol, 0.
53 parts by weight of 05N hydrochloric acid was gradually added dropwise to carry out hydrolysis. After aging this solution at 0°C for 24 hours, 164 parts by weight of trimethylolpropane triglycidyl ether (100 MF'' manufactured by Kyoeisha Yushi Co., Ltd.) and 5 parts by weight of magnesium perchlorate were added at room temperature and stirred. To this, flow control agent L-7 was applied.
The paint was adjusted by adding a few drops of 604. The lens processing and coating methods were the same as in Example-1.
実施例−３
ジメチルジメトキシシラン７９重量部、イソプロパツー
ル分散コロイダルシリカ＜触媒化成工業（株）製”０８
ＣＡＤ−１４３２”、固形分濃度６０％） １７ ｓ
重量部およびイソプロパツール５１２重量部からなる溶
液に、０．０５ Ｎ塩酸２８重量部を徐々に滴下し、加
水分解を行なった。この溶液を０℃で２４時間熟成した
後、トリメチロールプロパントリグリシジルエーテル（
共栄社油脂（株）製“エポライ）１０［ＩＭＦ”）１９
９重量部と過塩素酸マグネシウム７ｔを加え、攪拌して
均一とした。これに７０−コンドロール剤Ｌ−７６０４
を加えて塗料を調整した◇レンズの処理および塗布の方
法は実施例−１と同じである◇
実施例−４
γ−グリシドキシプロビルトリメトキシシラン２０７重
量部、水分散コロイダルシリカ（０産化学工業（株）製
１スノーテックスＣ″、固形分濃度２０％）２６３重１
１部およびメチルセロソルブ３６６重量部からなる溶液
に、００５Ｎ塩酸５７重量部を徐々に滴下し加水分解を
行なった。この溶液を０℃で２４時間熟成した後、１，
６−ヘキサンシオールジグリシジルエーテル（共栄社油
脂昧）製１エボライ）１６００”）１０１重量部と過塩
素酸マグネシウム６重量部を室温で加え、攪拌して均一
とした・これに、フローコントロール剤り−７６０４を
加えて塗料を調整した。レンズの処理および塗布の方法
は実施例−１と同じである。Example-3 79 parts by weight of dimethyldimethoxysilane, isopropanol-dispersed colloidal silica <manufactured by Catalysts & Chemicals Co., Ltd."08
CAD-1432”, solid content concentration 60%) 17 s
28 parts by weight of 0.05 N hydrochloric acid was gradually added dropwise to a solution consisting of 512 parts by weight of 0.05 N hydrochloric acid to effect hydrolysis. After aging this solution at 0°C for 24 hours, trimethylolpropane triglycidyl ether (
“Epolai) 10 [IMF”) 19 manufactured by Kyoeisha Yushi Co., Ltd.
9 parts by weight and 7 tons of magnesium perchlorate were added and stirred to make it homogeneous. This includes 70-chondrol agent L-7604.
◇The lens treatment and coating methods were the same as in Example-1◇Example-4 207 parts by weight of γ-glycidoxyprobyltrimethoxysilane, water-dispersed colloidal silica (0-product) 1 Snowtex C″ manufactured by Kagaku Kogyo Co., Ltd., solid content concentration 20%) 263 weight 1
57 parts by weight of 005N hydrochloric acid was gradually added dropwise to a solution consisting of 1 part by weight and 366 parts by weight of methyl cellosolve to effect hydrolysis. After aging this solution at 0°C for 24 hours, 1,
101 parts by weight of 6-hexanesiol diglycidyl ether (Kyoeisha Yushibai 1 Evolai 1600") and 6 parts by weight of magnesium perchlorate were added at room temperature and stirred to make it homogeneous. To this, a flow control agent was added. 7604 was added to adjust the paint.The lens treatment and coating method were the same as in Example-1.
実施例−５
γ−グリシドキシプロビルトリメトキシシラン２４９重
量部、コロイダルシリカ（日産化学（株）製１メタノー
ルシリカゾル２、固形分濃度３０％）１２Ｓ重量部およ
びメチルセロソルブ４６４重量部からなる溶液に、００
５Ｎ塩酸６−８重量部を徐々に滴下し加水分解を行なっ
た。この溶液をｏ’ａで２４時間熟成した後、グリセリ
ンジグリシジルエーテル（長潮産業（株）製“ブナコー
ルＥＸ５１３”）８６重量部と過塩素酸マグネシウム７
重量部を室温で加え、攪拌して均一とした。これに・７
０−コン）０−ル剤Ｌ−７６０４を加えて塗料を調整し
た。レンズの処理および塗布の方法は実施例−１と同じ
である〇
実施例−６
γ−グリシドキシプロビルトリメトキシシラン２１９重
量部、イソプロパ／−ル分散コロイダルシリカ（触媒化
成工業（株）製”Ｏ８（！ＡＬ−１４５２” 、固形分
濃度３０％）１１１重量部およびイソプロパツール４９
１重量部からなる溶液に、０、０５ Ｎ塩酸６０重量部
を徐々に滴下し加水分解を行なった。この溶液を０℃で
２４時間熟成した後、プロピレングリコールジグリシジ
ルエーテル（長ｉ１１産業（株）製”ｆ−１−：＝＋−
ルｌＸ９１１ ＃ ）１１２重量部および過塩素酸マグ
ネシウム７重量部を加え、攪拌して均一とした。これに
、フローコントロール剤Ｌ−７６０４を加えて塗料を調
整した。レンズの処理および塗布の方法は実施例−１と
同じである。Example-5 A solution consisting of 249 parts by weight of γ-glycidoxyprobyltrimethoxysilane, 12S parts by weight of colloidal silica (Nissan Chemical Co., Ltd. 1 methanol silica sol 2, solid content concentration 30%) and 464 parts by weight of methyl cellosolve. ni, 00
Hydrolysis was carried out by gradually dropping 6-8 parts by weight of 5N hydrochloric acid. After aging this solution in o'a for 24 hours, 86 parts by weight of glycerin diglycidyl ether ("Bunacol EX513" manufactured by Nagashio Sangyo Co., Ltd.) and 7 parts by weight of magnesium perchlorate were added.
Parts by weight were added at room temperature and stirred to homogenize. To this・7
0-Con) The paint was prepared by adding O-L agent L-7604. The lens treatment and coating methods are the same as in Example-1. Example-6 219 parts by weight of γ-glycidoxypropyltrimethoxysilane, isopropyl-dispersed colloidal silica (manufactured by Catalysts Kasei Kogyo Co., Ltd.) "O8 (!AL-1452", solid content concentration 30%) 111 parts by weight and isopropanol 49
To a solution consisting of 1 part by weight, 60 parts by weight of 0.05 N hydrochloric acid was gradually added dropwise to effect hydrolysis. After aging this solution at 0°C for 24 hours, propylene glycol diglycidyl ether (manufactured by Choi11 Sangyo Co., Ltd.)
112 parts by weight of LX911#) and 7 parts by weight of magnesium perchlorate were added and stirred to homogenize. Flow control agent L-7604 was added to this to prepare a paint. The lens processing and coating methods were the same as in Example-1.
実施例−７
γ−グリシドキシプｐピルメチルジェトキシシラン１７
４重量部、水分散コロイダルシリカ（触媒化成工業（株
）製” ０ａｔａｌｌｏｔｄ ＳＩＪ ” 、固形分
濃度２０％）３５１重量部およびメチルセロソルブ３３
１重量部からなる溶液に、００５Ｎ塩酸３０重量部を徐
々に滴下して加水分解を行なった。Example-7 γ-glycidoxypylmethyljethoxysilane 17
4 parts by weight, 351 parts by weight of water-dispersed colloidal silica ("0atallotd SIJ" manufactured by Catalysts & Chemicals Co., Ltd., solid content concentration 20%), and 33 parts by weight of methyl cellosolve
Hydrolysis was carried out by gradually dropping 30 parts by weight of 005N hydrochloric acid into a solution consisting of 1 part by weight.
この溶液を０℃で２４時間熟成した後、プロピレングリ
コールジグリシジルエーテル（長潮産業（株）製１デナ
コール１！！Ｘ９１１”）１０８重量部と過塩素酸マグ
ネシウム６重量部を加え、攪拌して均一とした０これに
１さらに７０−コンドロール剤Ｌ−７６０４を加えて塗
料を調整した。レンズの処理および塗布の方法は実施例
−１と同じである。After aging this solution at 0°C for 24 hours, 108 parts by weight of propylene glycol diglycidyl ether (1Denacol 1!! A coating material was prepared by adding 70-chondrol agent L-7604 to 0. The lens treatment and coating method were the same as in Example-1.
実施例−８
β−（３，４−エポキシシクロヘキシル）エチルトリメ
トキシシラン１３３重量部、コロイダル □シリカ
（日産化学（株）製１メタノールシリカゾル”固形分濃
度３０％）２１５重量部およびイソプロパノニル４７０
重量部からなる溶液に、０．０５Ｎ塩酸３５重量部を徐
々に滴下し加水分解を行なった０この溶液を０℃で２４
時間熟成した後、グ１ノセリントリグリシジルエーテル
（長潮産業＠） 製１デナ：ｌ−ルＩｃｘ５１４１）’
１４０重量部と過塩素酸マグネシウム７重量部を加え、
攪拌して均一とした。これに、フローコントロール剤Ｌ
−７６０４を加えて塗料を調整したＯレンズの処理およ
び塗布の方法は実施例−１と同じである。Example-8 133 parts by weight of β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 215 parts by weight of colloidal silica (1 methanol silica sol manufactured by Nissan Chemical Co., Ltd., solid content concentration 30%), and 470 parts by weight of isopropanonyl
35 parts by weight of 0.05N hydrochloric acid was gradually added dropwise to a solution consisting of parts by weight to perform hydrolysis.This solution was heated at 0°C for 24 hours.
After aging for an hour, G1-nocerin triglycidyl ether (Nagao Sangyo @) 1 dena: l-le Icx5141)'
Add 140 parts by weight and 7 parts by weight of magnesium perchlorate,
Stir to make it homogeneous. Add to this flow control agent L
The treatment and coating method for the O lens whose paint was adjusted by adding -7604 was the same as in Example-1.
比較例−１
γ−グリシドキシプロビルメチルジェトキシシラン７１
重量部に、攪拌しながら００５Ｎ塩酸１０重量部を加え
、ざらに１時間攪拌した後、室温で２４時間熟成したＯ
この液に、コロイダルシリカ（日産化学（株）製１メタ
ノールシリカゾル”、固形分源１度６０％）１６７重量
部、アルミニウムアセチルアセトネート４．５重量部、
さらにフローコントロール剤Ｌ−７６０４を０８１重量
部およびフェニルセロソルブ１２．４重量部を加えて、
攪拌し塗料を調整したＯレンズの処理および塗布の方法
は実施例−１と同じであや。Comparative example-1 γ-glycidoxypropylmethyljethoxysilane 71
To the part by weight, 10 parts by weight of 005N hydrochloric acid was added with stirring, and after roughly stirring for 1 hour, the O
To this liquid, 167 parts by weight of colloidal silica (1 methanol silica sol manufactured by Nissan Chemical Co., Ltd., solid content source 1% 60%), 4.5 parts by weight of aluminum acetylacetonate,
Furthermore, 081 parts by weight of flow control agent L-7604 and 12.4 parts by weight of phenyl cellosolve were added,
The method of treatment and application of the O-lens, in which the paint was adjusted by stirring, was the same as in Example-1.
比較例−２
イソプ四ピルアルコール７ （Ｓ、 ｓ 重量Ｈにγ−
グリシドキシプロビルトリメトキシシラン９８．８重量
部、ジメチルジメトキシシラン２８．４重量部を溶解し
、さらに０．１Ｎ塩酸４６．６重量部を徐々に加えて加
水分解を行ない、その後室温で２４時間熟成した◇この
溶液２４０重量部にエチルセロソルブ８８．４重量部、
過塩素機アンモニウＡ ［１，４２重量部および７０−
コン）ｏ−ル剤を添加して、均一とし塗料を調整した。Comparative Example-2 Isopropyl alcohol 7 (S, s γ- to weight H
98.8 parts by weight of glycidoxypropyltrimethoxysilane and 28.4 parts by weight of dimethyldimethoxysilane were dissolved, and 46.6 parts by weight of 0.1N hydrochloric acid was gradually added to carry out hydrolysis, followed by 24 parts by weight at room temperature. ◇To 240 parts by weight of this solution, 88.4 parts by weight of ethyl cellosolve,
Perchlorinator Ammonium A [1,42 parts by weight and 70-
Con) An oil agent was added to make the paint uniform.
レンズの処理および塗布の方法は実施例−１と同じであ
る。The lens processing and coating methods were the same as in Example-1.
Claims (1)
（０）及び（Ｄ）（式中１１は炭素数１〜６の炭イヒ水
素基、ビニル基、メタクリロキシ基また＆まエポキシ基
を有する有機基、Ｒ２は炭素数１〜４の炭イヒ水素基
Ｒ３は炭素数１〜５の炭イし水素基。 アルコキシルアルキル基または水素原子、２は０または
１を表わす）で示される有機ケイ素化合物の１種もしく
は２種以上、 （Ｂ）粒径１〜１００ミリミクロンのコロイダルシリカ （０） 多官能性エポキシ化合物 （Ｄ）過塩素酸マグネシウム を主原料としてなるハードコート膜を施した事を特徴と
する合成樹脂製レンズ０[Claims] The following (A) I (B) I is provided on the surface of the synthetic resin lens.
(0) and (D) (in the formula, 11 is an organic group having a carbon number of 1 to 6 carbon atoms, a vinyl group, a methacryloxy group, or an epoxy group; R2 is a carbon number of 1 to 4 carbon atoms)
R3 is a hydrocarbon group having 1 to 5 carbon atoms. (B) Colloidal silica with a particle size of 1 to 100 millimicrons (0) Polyfunctional epoxy compound (D) Synthetic resin lens 0 characterized by being coated with a hard coat film made of magnesium perchlorate as the main raw material
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58106092A JPS59231501A (en) | 1983-06-14 | 1983-06-14 | Plastic lens |
| FR8408768A FR2548389B1 (en) | 1983-06-14 | 1984-06-05 | SYNTHETIC RESIN LENS |
| US06/619,890 US4525421A (en) | 1983-06-14 | 1984-06-12 | Surface hard coat for a synthetic resin lens |
| DE3421953A DE3421953A1 (en) | 1983-06-14 | 1984-06-13 | SYNTHETIC RESIN LENS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58106092A JPS59231501A (en) | 1983-06-14 | 1983-06-14 | Plastic lens |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59231501A true JPS59231501A (en) | 1984-12-26 |
| JPH0459601B2 JPH0459601B2 (en) | 1992-09-22 |
Family
ID=14424898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58106092A Granted JPS59231501A (en) | 1983-06-14 | 1983-06-14 | Plastic lens |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4525421A (en) |
| JP (1) | JPS59231501A (en) |
| DE (1) | DE3421953A1 (en) |
| FR (1) | FR2548389B1 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62191802A (en) * | 1986-02-19 | 1987-08-22 | Toray Ind Inc | Transparent formed body and its production |
| US5622784A (en) * | 1986-01-21 | 1997-04-22 | Seiko Epson Corporation | Synthetic resin ophthalmic lens having an inorganic coating |
| US5759643A (en) * | 1987-01-16 | 1998-06-02 | Seiko Epson Corporation | Polarizing plate and method of production |
| US5783299A (en) * | 1986-01-21 | 1998-07-21 | Seiko Epson Corporation | Polarizer plate with anti-stain layer |
| JP2005172896A (en) * | 2003-12-08 | 2005-06-30 | Konica Minolta Opto Inc | Coating liquid for antireflection film formation and antireflection film |
| US6942924B2 (en) | 2001-10-31 | 2005-09-13 | Chemat Technology, Inc. | Radiation-curable anti-reflective coating system |
| WO2005121265A1 (en) * | 2004-06-11 | 2005-12-22 | Toray Industries, Inc. | Siloxane coating material, optical articles and process for the production of siloxane coating materials |
| JP2011006613A (en) * | 2009-06-26 | 2011-01-13 | Dainichiseika Color & Chem Mfg Co Ltd | Curable resin composition and hard coat film or sheet |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0195493B1 (en) * | 1985-03-22 | 1993-03-24 | Toray Industries, Inc. | Transparent article and process for preparation thereof |
| US4975328A (en) * | 1987-09-22 | 1990-12-04 | Hoya Corporation | Process for producing polyurethane lens |
| US5278243A (en) * | 1992-01-14 | 1994-01-11 | Soane Technologies, Inc. | High impact resistant macromolecular networks |
| JP2862576B2 (en) * | 1989-08-14 | 1999-03-03 | 日産自動車株式会社 | Cationic electrodeposition coating composition |
| US5104692A (en) * | 1990-04-20 | 1992-04-14 | Pilkington Visioncare Holdings, Inc. | Two-layer antireflective coating applied in solution |
| US5385955A (en) * | 1992-11-05 | 1995-01-31 | Essilor Of America, Inc. | Organosilane coating composition for ophthalmic lens |
| FR2718143B1 (en) * | 1994-03-29 | 1996-11-29 | Saint Gobain Vitrage | Composition for a non-wettable coating. |
| US5648407A (en) * | 1995-05-16 | 1997-07-15 | Minnesota Mining And Manufacturing Company | Curable resin sols and fiber-reinforced composites derived therefrom |
| US6233063B1 (en) | 1995-06-29 | 2001-05-15 | Agfa Corporation | Two lens converging device in a dual plane flat-bed scanning system |
| US5580606A (en) * | 1995-10-06 | 1996-12-03 | Singapore Institute Of Standards Etc. | Method for forming interference anti-reflective coatings by plasma surface modification |
| JP3712561B2 (en) * | 1999-03-30 | 2005-11-02 | Ｈｏｙａ株式会社 | Optical member having cured coating |
| US20030165015A1 (en) * | 2001-12-05 | 2003-09-04 | Ocular Sciences, Inc. | Coated contact lenses and methods for making same |
| US6984262B2 (en) * | 2003-07-16 | 2006-01-10 | Transitions Optical, Inc. | Adhesion enhancing coating composition, process for using and articles produced |
| US8361946B2 (en) * | 2004-04-08 | 2013-01-29 | Akzo Nobel N.V. | Detergent composition |
| ATE441125T1 (en) * | 2004-07-28 | 2009-09-15 | Novartis Ag | WATER-BASED INKS FOR HYDROGEL LENSES |
| JP4896004B2 (en) * | 2005-03-03 | 2012-03-14 | 株式会社ニコン・エシロール | Spectacle lens and method for processing spectacle lens |
| US20090081463A1 (en) * | 2007-09-21 | 2009-03-26 | Ppg Industries Ohio, Inc. | Tinted article having a high refractive index |
| EP2364337B1 (en) * | 2008-12-05 | 2020-04-22 | Coatings Foreign IP Co. LLC | Self-assembled silica condensates |
| US10234601B2 (en) | 2014-04-24 | 2019-03-19 | Hoya Lens Thailand Ltd. | Spectacle lens |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53420B2 (en) * | 1972-11-04 | 1978-01-09 | ||
| JPS5315743B2 (en) * | 1973-08-14 | 1978-05-26 | ||
| US3986997A (en) * | 1974-06-25 | 1976-10-19 | Dow Corning Corporation | Pigment-free coating compositions |
| JPS534020B2 (en) * | 1974-09-05 | 1978-02-13 | ||
| US4343857A (en) * | 1978-08-23 | 1982-08-10 | Goodyear Aerospace Corporation | Coatings for optical systems |
| JPS5540743A (en) * | 1978-09-19 | 1980-03-22 | Mitsubishi Gas Chem Co Inc | Surface treatment of polycarbonate resin molded article |
| DE3034524A1 (en) * | 1979-09-28 | 1981-04-16 | Daicel Chemical Industries, Ltd., Sakai, Osaka | Priming and top coating polycarbonate moulding - with hydrolysed partial condensates of alkyl and phenyl tri:alkoxy silane cpds. |
| US4478909A (en) * | 1980-10-24 | 1984-10-23 | Toray Industries, Inc. | Anti-fogging coating film |
| US4311762A (en) * | 1980-10-24 | 1982-01-19 | Corning Glass Works | Plastic components of improved hardness and scratch resistance |
| JPS57158235A (en) * | 1981-03-26 | 1982-09-30 | Toray Ind Inc | Plastic molding |
-
1983
- 1983-06-14 JP JP58106092A patent/JPS59231501A/en active Granted
-
1984
- 1984-06-05 FR FR8408768A patent/FR2548389B1/en not_active Expired
- 1984-06-12 US US06/619,890 patent/US4525421A/en not_active Expired - Lifetime
- 1984-06-13 DE DE3421953A patent/DE3421953A1/en active Granted
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5622784A (en) * | 1986-01-21 | 1997-04-22 | Seiko Epson Corporation | Synthetic resin ophthalmic lens having an inorganic coating |
| US5783299A (en) * | 1986-01-21 | 1998-07-21 | Seiko Epson Corporation | Polarizer plate with anti-stain layer |
| JPS62191802A (en) * | 1986-02-19 | 1987-08-22 | Toray Ind Inc | Transparent formed body and its production |
| JPH0451802B2 (en) * | 1986-02-19 | 1992-08-20 | Toray Industries | |
| US5759643A (en) * | 1987-01-16 | 1998-06-02 | Seiko Epson Corporation | Polarizing plate and method of production |
| US6942924B2 (en) | 2001-10-31 | 2005-09-13 | Chemat Technology, Inc. | Radiation-curable anti-reflective coating system |
| JP2005172896A (en) * | 2003-12-08 | 2005-06-30 | Konica Minolta Opto Inc | Coating liquid for antireflection film formation and antireflection film |
| WO2005121265A1 (en) * | 2004-06-11 | 2005-12-22 | Toray Industries, Inc. | Siloxane coating material, optical articles and process for the production of siloxane coating materials |
| JPWO2005121265A1 (en) * | 2004-06-11 | 2008-04-10 | 東レ株式会社 | Siloxane-based paint, optical article, and method for producing siloxane-based paint |
| JP2011006613A (en) * | 2009-06-26 | 2011-01-13 | Dainichiseika Color & Chem Mfg Co Ltd | Curable resin composition and hard coat film or sheet |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3421953A1 (en) | 1984-12-20 |
| FR2548389B1 (en) | 1987-04-10 |
| DE3421953C2 (en) | 1989-11-30 |
| JPH0459601B2 (en) | 1992-09-22 |
| US4525421A (en) | 1985-06-25 |
| FR2548389A1 (en) | 1985-01-04 |
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